Synthesis of 1,3-dihydro-5(r)-7,8-ethylenedioxy-2h-1,4-benzo-diazepin-2-ones

et al. 2007

Chem Heterocycl Compd

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Section: Ohmentioning

confidence: 68%

4H-3,1-benzoxazines from o-aminoacylbenzenes

Gazzaeva

et al. 2007

Chem Heterocycl Compd

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“…Reduced iron (17 g) was added to a solution of 6-acetyl-7-nitro-1,4-benzodioxane (2.23 g, 10 mmol) in benzene (100 ml) heated to 75°C and stirred at this temperature for 30 min, then water (7 ml) was added in portions over 2 h. The reaction mixture was stirred for 1 h at 80°C, the hot benzene solution was decanted, the solvent was evaporated, and the residue was recrystallized from ethanol. Yield 79%; mp 126-127°C [37].…”

Section: Methodsmentioning

confidence: 99%

A new effective route for the synthesis of substituted 2h-indazoles

Трофимова

et al. 2009

Chem Heterocycl Comp

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A two-stage synthesis of 2H-indazoles has been established, based on consecutive reactions of reduction of 2-alkyl-, 2-cyclopropyl-, and 2-arylcarbonylazobenzenes to phenylazo-substituted benzyl alcohols and intramolecular heterocyclization of the reduction products under the influence of organic acids.In recent years there has been a considerably strengthened interest in the synthesis and study of the medicobiological properties of derivatives of 2H-indazoles, resulting from the observation in a series of compounds which are seldom encountered in nature, a class of heterocycles with a wide range of biological activity: antiangiogenic [1], anticarcinogenic and anti-inflammatory [2,3], antimicrobial [4], antifungal [5,6], cytotoxic [7], and antihelminthic [8]. In addition compounds of this class show potential as inhibitors of NO-synthetases [9, 10], protein kinases [11,12], tubulin [13], modulators of X-receptors of the liver [14], and they also show properties of male contraceptives [15,16].The discovery of the biological activity of the 2H-indazoles caused the real problem of the synthesis of new derivatives of this class of heterocycles. It is important to underline that at present a wide range of precursors has been used to synthesize the 2H-indazole ring, in practice including all strategic routes for its synthesis. For example, 2H-indazoles have been synthesized from 2-azidobenzylideneamines [17] or 2-azidobenzoylamines [18,19], oxidative cyclization from N-acylhydrazones of 2-aminoacylbenzenes [20,21], reaction of carbenes with azobenzene [22,23], rearrangement of ortho-substituted azobenzenes [24,25], and reductive heterocyclization of ortho-nitrobenzylideneamines [26][27][28], and heterocyclization of ortho-nitrobenzylamines [29][30][31][32][33]. A variant of the formation of the 2H-indazole system from compounds containing the pyrazole unit have been described. For example, oxidation of 4,5-tetramethylenepyrazoles with dichlorodicyanobenzoquinone gave substituted 2H-indazoles in high yield [34]. However, despite the abundance of variants for the construction of the 2H-indazole ring, the variation of substituents is practically limited to those in positions 2 and 3, and only in the papers [30,31,33] were syntheses of 2H-indazoles containing substituents in the annelated benzene ring reported.

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“…6-Amino-7-cyclopropylcarbonyl-1,4-benzodioxane (1) and 6-amino-7-(m-fluorobenzoyl)-1,4-benzodioxane (2) were obtained by the reduction of the corresponding nitro compounds as described in our earlier work [9]. __________________________________________________________________________________________…”

mentioning

confidence: 99%

“…6-Amino-7-cyclopropylcarbonyl-1,4-benzodioxane (1) and 6-amino-7-(m-fluorobenzoyl)-1,4-benzodioxane (2) were obtained by the reduction of the corresponding nitro compounds as described in our earlier work [9]. 6-N-Phenacylamino-7-cyclopropylcarbonyl-1,4-benzodioxane (3) was obtained from amine 1 as described in our previous work [10] …”

mentioning

confidence: 99%

“…The solvent for 1-4 was CDCl 3 ; the residual protons of the deuterated solvent served as the internal standard. The solvent for 5 and 6 was DMSO-d 6 using TMS as the internal standard.6-Amino-7-cyclopropylcarbonyl-1,4-benzodioxane (1) and 6-amino-7-(m-fluorobenzoyl)-1,4-benzodioxane (2) were obtained by the reduction of the corresponding nitro compounds as described in our earlier work [9]. __________________________________________________________________________________________…”

mentioning

confidence: 99%

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A new synthetic pathway for 2-quinolones

2008

Chem Heterocycl Comp

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